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accessDimethyl(1,10-phenanthroline-κ2N,N′)bis(thiocyanato-κN)tin(IV)
aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: seikweng@um.edu.my
The SnIV atom in the title compound, [Sn(CH3)2(NCS)2(C12H8N2)], is located on a twofold rotation axis in a distorted octahedral enviroment. The methyl groups are trans to each other [C—Sn—C = 175.7 (3)°], whereas the thiocyanate groups are cis to each other.
Related literature
For dimethyltin dithiothiocyanate, see: Britton (2006![[Britton, D. (2006). Acta Cryst. C62, m93-m94.]](../../../../../../logos/arrows/e_arr.gif "Britton, D. (2006). Acta Cryst. C62, m93-m94.")
). For the 4,4′-bipyridine adduct, see: Najafi et al. (2011).
![[Scheme 1]](bt6862scheme1.gif)
Experimental
Crystal data
|
Data collection: CrysAlis PRO (Agilent, 2012); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
contains datablocks global, I. DOI: 10.1107/S1600536812047691/bt6862sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536812047691/bt6862Isup2.hkl
Dimethyltin dithiocyanate (0.27 g, 1 mmol) and 1,10-phenanthroline hydrate (0.19 g, 1 mmol) were loaded into a convection tube; the tube was filled with ethyl alcohol and kept at 333 K. Colorless crystals were collected from the side arm after several days.
Carbon-bound H-atoms were placed in calculated positions [C–H 0.93 to 0.96 Å, Uiso(H) 1.2 to 1.5Ueq(C)] and were included in the in the riding model approximation.
Data collection: CrysAlis PRO (Agilent, 2012); cell CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).
![[Figure 1]](./bt6862fig1thm.gif) | Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of (CH3)2Sn(NCS)2(C12H8N2) at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. |
| [Sn(CH3)2(NCS)2(C12H8N2)] | F(000) = 880 |
| Mr = 445.12 | Dx = 1.616 Mg m−3 |
| Orthorhombic, Pccn | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ab 2ac | Cell parameters from 1757 reflections |
| a = 6.8218 (7) Å | θ = 3.2–27.5° |
| b = 12.9272 (13) Å | µ = 1.63 mm−1 |
| c = 20.746 (2) Å | T = 295 K |
| V = 1829.5 (3) Å3 | Prism, colorless |
| Z = 4 | 0.30 × 0.15 × 0.05 mm |
| Agilent SuperNova Dual diffractometer with an Atlas detector | 2116 independent reflections |
| Radiation source: SuperNova (Mo) X-ray Source | 1368 reflections with I > 2σ(I) |
| Mirror monochromator | Rint = 0.055 |
| Detector resolution: 10.4041 pixels mm-1 | θmax = 27.6°, θmin = 3.2° |
| ω scan | h = −6→8 |
| Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −16→16 |
| Tmin = 0.641, Tmax = 0.923 | l = −27→24 |
| 10262 measured reflections |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
| wR(F2) = 0.106 | w = 1/[σ2(Fo2) + (0.0429P)2 + 0.5974P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.01 | (Δ/σ)max = 0.001 |
| 2116 reflections | Δρmax = 0.51 e Å−3 |
| 106 parameters | Δρmin = −0.63 e Å−3 |
| 0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0024 (4) |
| [Sn(CH3)2(NCS)2(C12H8N2)] | V = 1829.5 (3) Å3 |
| Mr = 445.12 | Z = 4 |
| Orthorhombic, Pccn | Mo Kα radiation |
| a = 6.8218 (7) Å | µ = 1.63 mm−1 |
| b = 12.9272 (13) Å | T = 295 K |
| c = 20.746 (2) Å | 0.30 × 0.15 × 0.05 mm |
| Agilent SuperNova Dual diffractometer with an Atlas detector | 2116 independent reflections |
| Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | 1368 reflections with I > 2σ(I) |
| Tmin = 0.641, Tmax = 0.923 | Rint = 0.055 |
| 10262 measured reflections |
| R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
| wR(F2) = 0.106 | H-atom parameters constrained |
| S = 1.01 | Δρmax = 0.51 e Å−3 |
| 2116 reflections | Δρmin = −0.63 e Å−3 |
| 106 parameters |
| x | y | z | Uiso*/Ueq | ||
| Sn1 | 0.7500 | 0.2500 | 0.243352 (18) | 0.04816 (19) | |
| S1 | 0.3311 (2) | 0.45584 (12) | 0.09896 (7) | 0.0957 (6) | |
| N1 | 0.5798 (5) | 0.3037 (3) | 0.33508 (16) | 0.0515 (8) | |
| N2 | 0.5246 (7) | 0.3231 (4) | 0.1785 (2) | 0.1073 (18) | |
| C1 | 0.5903 (7) | 0.1114 (4) | 0.2395 (2) | 0.0746 (14) | |
| H1A | 0.6337 | 0.0710 | 0.2034 | 0.112* | |
| H1B | 0.4533 | 0.1267 | 0.2349 | 0.112* | |
| H1C | 0.6109 | 0.0731 | 0.2786 | 0.112* | |
| C2 | 0.4146 (7) | 0.3576 (4) | 0.3337 (3) | 0.0736 (14) | |
| H2 | 0.3600 | 0.3748 | 0.2941 | 0.088* | |
| C3 | 0.3208 (10) | 0.3891 (5) | 0.3898 (4) | 0.107 (2) | |
| H3 | 0.2060 | 0.4276 | 0.3875 | 0.128* | |
| C4 | 0.3969 (12) | 0.3635 (6) | 0.4470 (4) | 0.115 (3) | |
| H4 | 0.3327 | 0.3832 | 0.4846 | 0.138* | |
| C5 | 0.5721 (10) | 0.3073 (5) | 0.4510 (3) | 0.0882 (18) | |
| C6 | 0.6600 (6) | 0.2783 (3) | 0.3924 (2) | 0.0556 (11) | |
| C7 | 0.6688 (15) | 0.2767 (9) | 0.5097 (3) | 0.142 (5) | |
| H7 | 0.6135 | 0.2956 | 0.5490 | 0.170* | |
| C8 | 0.4443 (7) | 0.3778 (4) | 0.1449 (2) | 0.0644 (12) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Sn1 | 0.0574 (3) | 0.0459 (3) | 0.0411 (3) | 0.00503 (18) | 0.000 | 0.000 |
| S1 | 0.1188 (12) | 0.0817 (11) | 0.0866 (11) | 0.0168 (9) | −0.0541 (9) | −0.0028 (8) |
| N1 | 0.056 (2) | 0.043 (2) | 0.055 (2) | 0.0032 (17) | 0.0090 (16) | −0.0054 (17) |
| N2 | 0.127 (4) | 0.085 (4) | 0.110 (4) | 0.010 (3) | −0.058 (3) | 0.019 (3) |
| C1 | 0.081 (4) | 0.065 (3) | 0.078 (4) | −0.010 (3) | −0.014 (2) | −0.009 (3) |
| C2 | 0.062 (3) | 0.054 (3) | 0.105 (4) | 0.005 (2) | 0.023 (3) | −0.010 (3) |
| C3 | 0.085 (4) | 0.075 (4) | 0.161 (7) | −0.002 (3) | 0.061 (5) | −0.028 (5) |
| C4 | 0.137 (6) | 0.096 (5) | 0.113 (6) | −0.044 (5) | 0.087 (5) | −0.050 (5) |
| C5 | 0.123 (5) | 0.082 (4) | 0.059 (3) | −0.039 (4) | 0.038 (3) | −0.022 (3) |
| C6 | 0.071 (3) | 0.052 (3) | 0.044 (2) | −0.021 (2) | 0.014 (2) | −0.008 (2) |
| C7 | 0.225 (15) | 0.156 (12) | 0.044 (3) | −0.092 (10) | 0.035 (4) | −0.019 (4) |
| C8 | 0.071 (3) | 0.068 (3) | 0.054 (3) | −0.001 (3) | −0.015 (2) | −0.009 (2) |
| Sn1—C1 | 2.098 (5) | C1—H1C | 0.9600 |
| Sn1—C1i | 2.098 (5) | C2—C3 | 1.388 (8) |
| Sn1—N2i | 2.251 (4) | C2—H2 | 0.9300 |
| Sn1—N2 | 2.251 (4) | C3—C4 | 1.337 (10) |
| Sn1—N1 | 2.335 (3) | C3—H3 | 0.9300 |
| Sn1—N1i | 2.335 (3) | C4—C5 | 1.401 (9) |
| S1—C8 | 1.588 (5) | C4—H4 | 0.9300 |
| N1—C2 | 1.326 (5) | C5—C6 | 1.405 (6) |
| N1—C6 | 1.350 (5) | C5—C7 | 1.442 (9) |
| N2—C8 | 1.134 (5) | C6—C6i | 1.430 (9) |
| C1—H1A | 0.9600 | C7—C7i | 1.31 (2) |
| C1—H1B | 0.9600 | C7—H7 | 0.9300 |
| C1—Sn1—C1i | 175.7 (3) | Sn1—C1—H1C | 109.5 |
| C1—Sn1—N2i | 88.48 (19) | H1A—C1—H1C | 109.5 |
| C1i—Sn1—N2i | 88.94 (18) | H1B—C1—H1C | 109.5 |
| C1—Sn1—N2 | 88.94 (18) | N1—C2—C3 | 121.9 (6) |
| C1i—Sn1—N2 | 88.48 (19) | N1—C2—H2 | 119.1 |
| N2i—Sn1—N2 | 106.6 (3) | C3—C2—H2 | 119.1 |
| C1—Sn1—N1 | 91.51 (16) | C4—C3—C2 | 119.5 (7) |
| C1i—Sn1—N1 | 92.01 (15) | C4—C3—H3 | 120.2 |
| N2i—Sn1—N1 | 162.09 (16) | C2—C3—H3 | 120.2 |
| N2—Sn1—N1 | 91.30 (17) | C3—C4—C5 | 120.7 (6) |
| C1—Sn1—N1i | 92.01 (15) | C3—C4—H4 | 119.6 |
| C1i—Sn1—N1i | 91.51 (16) | C5—C4—H4 | 119.6 |
| N2i—Sn1—N1i | 91.30 (17) | C4—C5—C6 | 116.9 (6) |
| N2—Sn1—N1i | 162.09 (16) | C4—C5—C7 | 125.6 (6) |
| N1—Sn1—N1i | 70.80 (18) | C6—C5—C7 | 117.6 (7) |
| C2—N1—C6 | 119.4 (4) | N1—C6—C5 | 121.6 (5) |
| C2—N1—Sn1 | 124.2 (3) | N1—C6—C6i | 118.2 (2) |
| C6—N1—Sn1 | 116.4 (3) | C5—C6—C6i | 120.2 (4) |
| C8—N2—Sn1 | 163.6 (5) | C7i—C7—C5 | 122.2 (4) |
| Sn1—C1—H1A | 109.5 | C7i—C7—H7 | 118.9 |
| Sn1—C1—H1B | 109.5 | C5—C7—H7 | 118.9 |
| H1A—C1—H1B | 109.5 | N2—C8—S1 | 178.8 (5) |
| C1—Sn1—N1—C2 | −89.4 (4) | Sn1—N1—C2—C3 | −178.9 (4) |
| C1i—Sn1—N1—C2 | 88.1 (4) | N1—C2—C3—C4 | −0.9 (9) |
| N2i—Sn1—N1—C2 | −179.2 (5) | C2—C3—C4—C5 | 1.4 (10) |
| N2—Sn1—N1—C2 | −0.5 (4) | C3—C4—C5—C6 | −1.1 (9) |
| N1i—Sn1—N1—C2 | 179.0 (4) | C3—C4—C5—C7 | 179.2 (8) |
| C1—Sn1—N1—C6 | 91.6 (3) | C2—N1—C6—C5 | 0.2 (6) |
| C1i—Sn1—N1—C6 | −90.9 (3) | Sn1—N1—C6—C5 | 179.3 (3) |
| N2i—Sn1—N1—C6 | 1.8 (6) | C2—N1—C6—C6i | −178.9 (4) |
| N2—Sn1—N1—C6 | −179.5 (3) | Sn1—N1—C6—C6i | 0.1 (6) |
| N1i—Sn1—N1—C6 | 0.0 (2) | C4—C5—C6—N1 | 0.3 (7) |
| C1—Sn1—N2—C8 | −167.4 (17) | C7—C5—C6—N1 | −180.0 (6) |
| C1i—Sn1—N2—C8 | 9.2 (17) | C4—C5—C6—C6i | 179.4 (5) |
| N2i—Sn1—N2—C8 | −79.3 (17) | C7—C5—C6—C6i | −0.8 (9) |
| N1—Sn1—N2—C8 | 101.1 (17) | C4—C5—C7—C7i | 179.3 (13) |
| N1i—Sn1—N2—C8 | 99.4 (17) | C6—C5—C7—C7i | −0.5 (19) |
| C6—N1—C2—C3 | 0.0 (7) |
| Symmetry code: (i) −x+3/2, −y+1/2, z. |
Experimental details
| Crystal data | |
| Chemical formula | [Sn(CH3)2(NCS)2(C12H8N2)] |
| Mr | 445.12 |
| Crystal system, space group | Orthorhombic, Pccn |
| Temperature (K) | 295 |
| a, b, c (Å) | 6.8218 (7), 12.9272 (13), 20.746 (2) |
| V (Å3) | 1829.5 (3) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 1.63 |
| Crystal size (mm) | 0.30 × 0.15 × 0.05 |
| Data collection | |
| Diffractometer | Agilent SuperNova Dual diffractometer with an Atlas detector |
| Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2012) |
| Tmin, Tmax | 0.641, 0.923 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 10262, 2116, 1368 |
| Rint | 0.055 |
| (sin θ/λ)max (Å−1) | 0.651 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.106, 1.01 |
| No. of reflections | 2116 |
| No. of parameters | 106 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.51, −0.63 |
Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).
Acknowledgements
We thank Shahid Beheshti University and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.
References
Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Britton, D. (2006). Acta Cryst. C62, m93–m94. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Najafi, E., Amini, M. M. & Ng, S. W. (2011). Acta Cryst. E67, m350. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
Few amine adducts of dimethyltin dithiocyanate, which exists as a weakly bridged polymeric chain (Britton, 2006), have been reported. The 4,4'-bipyridine adduct is polymeric (Najafi et al., 2011). In the 1,10-phenanthroline adduct (Scheme I, Fig. 1), the SnIV atom is located on a twofold rotation axis in an octahedral enviroment. The methyl groups are trans to each other whereas the thiocyanate groups are cis to each other.